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Your Next Steps

Shadow at Chesterton

  • Prospective students are encouraged to spend a full shadow day at Chesterton Academy.

  • Students are paired with an Ambassador to experience our classes and joyful atmosphere.

  • Contact our office to schedule a time that's convenient for you.

Attend an Open House 

  • Parents and students are invited to attend an Open House at our campus.

  • You'll meet our faculty and students, learn about our curriculum, and explore our sports and other student activities.

  • RSVP for an Open House.

Apply and Enroll

  • Our application process is completed online through TADS.

  • After the online application is complete, our headmaster will meet one-on-one with you and your student to get to know you and answer any questions that you may have.

An Affordable Education

Tuition & Fees

Chesterton Academy is committed to offering an outstanding high school education at an affordable cost to families. Tuition for the 2018-19 academic year is $7,300, with a $350 student fee. A $500 non-refundable deposit which is due upon enrollment which will be applied  toward your tuition.

Because tuition does not cover the full cost of an education at Chesterton, families are expected to aid in fundraising efforts throughout the year.


Financial Aid

Scholarships and tuition assistance are available to families who apply and qualify for aid. The student application process must be completed in full before being considered for tuition assistance.

To complete the financial aid assessment on TADS, click here.

Placement Exam


All students are required to take a placement exam as part of the application and enrollment process. The placement exam is used as a diagnostic tool to ensure students are placed in the appropriate section of math, and to help identify areas of academic strengths and opportunities for growth.

Chesterton Academy administers the Scholastic Testing High School Placement Test as its placement exam for incoming freshmen. This is the same placement test used by other private high schools in the area. We accept a copy of test results from other schools.


Admissions Events

Frequently Asked Questions

Life at Chesterton Academy

+ Is Chesterton Academy a Catholic School?

Chesterton Academy of Milwaukee is a non-diocesan, 501(c)(3) non-profit, private high school administered and staffed by Catholic lay persons and incorporated under the laws of Wisconsin. Independent of the Diocese of Milwaukee, the school is not an agency of and is in not connected or affiliated with the Diocese of Milwaukee. However, as faithful, practicing Catholics, the school board, administrators and teachers joyfully sign an oath of fidelity to the Magisterium and a profession of faith to the Catholic Church. Chesterton Academy of Milwaukee is a member of the Chesterton Schools Network, a network of high schools all using the Cardinal Newman Society award-winning integrated, classical curriculum from the founding school in Edina, Mn.

  • Chesterton Academy in Milwaukee does not claim to bear the name “Catholic” school (cf. canon 803). It is a private school based on the initiatives of parents and individuals attracted to the classical education tradition. Those involved in establishing Chesterton Academy take seriously their duty and right to promote such an undertaking as affirmed by canon law in canon 216 “even by their own undertakings.” Faithful to the norm of canon 216 and 803, and always wishing to show deep respect toward our local archbishop, Chesterton Academy of Milwaukee does not claim to use the name “Catholic” and would only use the name “Catholic” with the consent of the competent ecclesiastical authority.
  • Chesterton Academy seeks to provide education for those families who are specifically attracted to an integrated, classical education deeply rooted in Catholic tradition. In fact, every school day includes daily Mass and all faculty members are required to take an oath of fidelity to the Magisterium as condition of employment.
  • Chesterton Academy does not seek to be in competition with other schools, but rather to provide another high school option for parents who in conscience have discerned that a rigorous classical education is the best way to fulfill their right and duty to educate their children (cf. canon 793 §1)

+ What's your DAILY SCHEDULE?

The school day at Chesterton Academy of Milwaukee begins at around 8:00 a.m. and ends at 3:30 p.m. Students begin their day at a nearby church for daily Mass, with an opportunity for confession on Thursdays at 7:45 a.m. and Adoration of the Blessed Sacrament after Mass on the first Friday of each month. Students are transported to the school via school bus for classes.

+ Do you accept TRANSFER STUDENTS?

Chesterton Academy welcomes transfer students each year who come from public, private, homeschool, and online high school environments. Our Academic Dean works closely with each transfer student to ensure their success as they transition to Chesterton.


Our students come from a wide range of educational backgrounds, including parochial K-8 schools, public schools, charter schools, homeschool, and online high schools.

+ How much HOMEWORK is assigned?

Chesterton Academy works to limit assigned homework to two hours of homework per evening. We seek to be efficient in the learning process such that students have time in the evenings to spend with their family and to commit to extracurricular activities and after-school jobs. We also build the class schedule to include three free periods per week to accommodate our students. They may use this time to study or to take a break as needed.

Preparing for Your First Day

+ What is your SCHOOL UNIFORM?

School uniforms can be ordered online or by phone from Donald's Uniform: Donald’s has their best sale of the year in June!

Keep in mind:

  • Blazers are mandatory for Mass and certain events.
  • Choir uniform is required.
  • Skirts may take up to 10 weeks.
  • Skirts may be ordered with no hem and an open bottom to hem to length needed when used.
  • Skirt measurement is from waist to mid knee, and most girls will require the LONG version.
  • Ladies fitted white shirt tends to run smaller.
  • Men’s pants should use a dress pant waist measurement.
  • Price Sheet: or call 651-776-2723 or 1-800-728-8082 – Ext. 1

The uniform consists of:


  • White short-sleeve or long-sleeve oxford shirt (fitted or reg.)
  • Navy pleated skirt, to mid-knee
  • Navy knee-highs
  • Solid black/brown dress flat shoes
  • Navy V-neck sweater vest or long-sleeve pullover sweater with school monogram (optional)
  • Navy blazer with school monogram


  • White short-sleeve or long-sleeve oxford shirt
  • Khaki flat or pleated-front pants
  • Crew socks
  • Solid black leather dress shoe (various options)
  • Navy V-neck sweater vest or long-sleeve pullover sweater with school monogram (optional)
  • Navy blazer with school monogram
  • Gold/navy striped tie
  • Black belt

The uniform should be clean and in good condition. Girls’ skirts must be at the knee; girls should take measurements to compare to the sizing charts from Donald’s Uniform to determine whether to order the regular or long length, accommodating for some growth. All students need to purchase a blazer. Sweaters and vests are optional. The following items must be purchased from Donald’s Uniform: girls’ skirts and girls shirts (regular or fitted), boy’s pants, blazers, sweaters, vests, and ties. Boys may purchase comparable oxford cloth dress shirts, belts and socks from other retailers. Girls may purchase navy socks from other sources.

Hair should be clean, neatly groomed, and must be a natural color, with boys’ hair above the eyebrows, ears and collar. Boys should be clean-shaven with sideburns no longer than the middle of the ear. Girls may wear light, natural-looking make-up, and clear or light pink nail polish is allowed. For boys and girls, no visible tattoos or piercings are allowed except girls may wear one stud in each earlobe (matching). Simple chain necklace with a religious significance and/or a scapular may be worn under the shirt for girls and boys.

+ How is LUNCH provided?

Students bring their own cold lunch and may use school microwave to heat meals.

+ How are HOUSES assigned?

On a first day of school, new students are assigned by the headmaster and are welcomed by their new housemates. Siblings are typically assigned to the same house, unless otherwise requested. Once a house has been chosen for a student, they will remain in that house until they graduate.

+ What is the SUMMER READING requirement?

Chesterton students are required to read one classical work over the summer each year. Reading assignments and study guides are available online. All students will have a quiz on their assigned book within the first week of the school year in their literature class.

+ What SCHOOL SUPPLIES are needed?

The school supply list is released in July together with details on summer reading assignments.